#ThrowbackThursday: An Incredibly Awkward Photo Of The “Fresh Prince” Cast With Hugh Hefner

The ’90s were rough on men’s fashion. Case in point: when Will Smith wore baseball shorts, socks and sandals to the Playboy Mansion to meet Hugh Hefner. His Fresh Prince of Bel-Air co-star Alfonso Ribeiro didn’t fare much better, unless of course it was a pajama party rather than a pool party, because at least then his boxer shorts/swim trunks would have been technically ok.

Karyn Parsons on the other hand, looked stunning as she always did back in those days.

There’s a lot going on in this picture, but let us never forget. Never forget what men wore in the ’90s. Never forget where Will Smith started from. And, inversely, never forget how long Hugh Hefner has been the man.

About the AuthorGreg Weinstein

In 1999, Greg launched Island Def Jam’s new media division, working with the record label to build the kind of Internet and social media infrastructure that every entertainment and media company takes for granted today. From there he brought his new media expertise and entertainment connections to the world of streetwear, serving as Marketing Director at Karmaloop and launching KarmaloopTV, a cutting edge project that bridged the gap between commerce and culture.
Thrillist Media Group then brought Greg to help grow the company’s presence in the world of cultural taste-making through the launch of its streetwear property, The Crosby Press.
Today, Greg serves as creative director at SlamXHype, one the most well-respected online publications in the streetwear space. Under his guidance, SlamXHype has experienced a renaissance in both influence and readership.